1,2-Dichloroethane → Methyl cis-2-(3-chloro-5-(5-(2-(methoxymethyl)-2'-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-ylamino)cyclopentanecarboxylate

HRID 1631042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631042
[Cl:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[C:18]([O:20][CH3:21])=[O:19])=[N:4][CH:5]=[C:6]([C:8](=[N:10][OH:11])[NH2:9])[CH:7]=1.Br[C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=O)=[CH:25][C:24]=1[CH2:33]OC.[CH2:36](Cl)[CH2:37]Cl>CC#N.N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[C:18]([O:20][CH3:21])=[O:19])=[N:4][CH:5]=[C:6]([C:8]2[N:9]=[C:33]([C:24]3[CH:23]=[CH:32][C:31]([C:5]4[CH:6]=[CH:7][CH:2]=[CH:3][C:36]=4[CH3:37])=[C:26]([CH2:27][O:29][CH3:30])[CH:25]=3)[O:11][N:10]=2)[CH:7]=1

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoateHCID 90293497cis-Methyl 2-(3-chloro-5-(n'-hydroxycarbamimidoyl)pyridin-2-ylamino)cyclopentanecarboxylate

Produkt 1

HCID 67135658Methyl cis-2-(3-chloro-5-(5-(2-(methoxymethyl)-2'-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-ylamino)cyclopentanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of cis-methyl 2-(3-chloro-5-(N′-hydroxycarbamimidoyl)pyridin-2-ylamino)cyclopentanecarboxylate (0.172 g; 0.55 mmol) and Intermediate A1 (0.155 g; 0.60 mmol) in MeCN (2 mL) was added EDC (0.117 g; 0.61 mmol). The reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with pyridine (2 mL) and heated at 150° C. in the microwave for 30 minutes. The solvent was removed in vacuo and the residue dissolved in DCM. The mixture was washed with water and the organic phase passed through a hydrophobic frit. The solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica, eluting with iso-hexane/EtOAc (4:1) to afford the title product. 1H NMR (CDCl3, 400 MHz) δ 8.84 (1H, d, J=2 Hz), 8.40 (1H, s), 8.21 (1H, d, J=2), 8.15-8.10 (1H, m), 7.34-7.26 (4H, m), 7.13 (1H, d, J=7.5 Hz), 5.91 (1H, d, J=8.3 Hz), 4.83 (1H, m), 4.22-4.13 (2H, m), 3.63 (3H, s), 3.33 (3H, s), 3.23-3.17 (1H, m), 2.21-1.63 (9H, m).

Aufarbeitung

  1. temperatureheated at 150° C. in the microwave for 30 minutes
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in DCM
  4. washThe mixture was washed with water
  5. customThe solvent was evaporated in vacuo
  6. customThe residue was purified by flash chromatography on silica
  7. washeluting with iso-hexane/EtOAc (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-fa2f0079e3c54211b6341510b726c5fa
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791142B2

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